In this episode of The Peak Season Podcast, Luke and Tyler break down real-world, low-effort strategies that directly increase short-term rental profit. Using recent bookings at White Birch Cabin as a case study, they explain how small system tweaks—like minimum stay adjustments, direct booking visibility, and smart upsells—can add thousands of dollars to the bottom line without adding operational stress. This episode is all about thinking like an operator, not just a host.

• How a single direct booking saved a guest $1,500 and added ~$2,000 in net profit
• Why savvy guests actively search for direct booking options
• Using automated messages and host signatures to create discovery
• Upsells that don’t feel like nickel-and-diming
• Leveraging tools like Hospitable for frictionless add-on revenue
• When welcome gifts protect pricing power and reviews
• Practical partnership ideas for rural and urban markets
• Why small revenue adds hit profit harder than headline ADR increases

00:00 – Intro & episode focus
00:24 – Breaking minimum stays to unlock demand
01:46 – How a guest found the direct booking site
02:27 – The math behind a $2,000 profit swing
03:45 – Direct bookings that wouldn’t exist on Airbnb
06:35 – Upsells without hurting the guest experience
07:45 – Psychology of “deep discounts”
10:57 – Automating upsells with Hospitable
13:39 – Grocery delivery & revenue sharing
15:17 – Firewood, s’mores kits, and value perception
17:40 – Welcome gifts vs. review impact
19:37 – Mid-stay cleans & local partnerships
22:02 – Transportation, charters, and guidebook monetization
24:09 – Final thoughts on profit-first thinking

You don’t need more nights to make more money—you need better systems. When you treat your short-term rental like a business, small optimizations compound fast, and nearly all of it drops straight to profit.

This podcast is for educational and informational purposes only. The strategies discussed are based on personal experience and may not apply to every market or situation. Listeners should evaluate their own properties, local regulations, and risk tolerance before implementing any strategies discussed.

🎙️ Episode Show Notes

Episode Title:

Evaluating a New STR Market from 30,000 Feet: The Bourbon Trail (Part 1)

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### Episode Description

In this episode of the Peak Season Podcast, Luke and Tyler step outside their usual Michigan focus and evaluate a brand-new short-term rental market: Kentucky’s Bourbon Trail. Rather than jumping straight into spreadsheets and underwriting, this episode intentionally stays at the 30,000-foot level—the phase where operators decide whether a market is even worth deeper analysis.

Luke and Tyler begin exactly where most guests do: the Airbnb home screen. By searching without dates and analyzing which listings surface first, they identify properties that are already winning, recurring amenities, and the types of guests the market attracts. A clear pattern emerges quickly—the Bourbon Trail is a group-driven, weekend-heavy market, dominated by friend trips, bachelor groups, and couples traveling together.

That insight drives everything else. Instead of tiny cabins or ultra-luxury builds, the most successful listings tend to fall in the 4–6 bedroom range, with flexible layouts and strong secondary living spaces like basements, garages, and lounges. Luke explains why review count and calendar behavior matter more than nightly rate, while Tyler adds firsthand guest experience from recent Bourbon Trail trips to ground the analysis in reality.

From there, the episode shifts from Airbnb to Zillow to test whether top-performing listings can realistically be replicated at today’s prices. They evaluate new construction, older ranch homes, rural properties with acreage, and value-add opportunities—always asking the same question: Can this realistically become a winning short-term rental?

A key theme throughout the episode is restraint. Not every market deserves underwriting. Before running numbers, investors should confirm they aren’t priced out, boxed in by regulations, limited by neighbors, or constrained by inventory. The Bourbon Trail passes that test, showing strong demand, attainable price points, and multiple viable strategies.

This is Part 1 of a two-part series. In the next episode, Luke and Tyler will underwrite two real properties—one lower-priced and one higher-priced—to compare cash-on-cash returns, revenue ceilings, and overall risk. If you want to understand how experienced operators decide where to invest before worrying about how much, this episode lays the foundation.

---

### Disclaimer

The information provided in this podcast is for educational and informational purposes only and should not be considered financial, legal, tax, or investment advice. Luke Miller and Tyler Kostich are not licensed financial advisors. All real estate investments carry risk, and results discussed on this show are not guaranteed. You should conduct your own due diligence and consult with qualified professionals before making any investment decisions.

In this episode of The Peak Season Podcast, Luke and Tyler return to PriceLabs for a hands-on walkthrough of one of the most underused (and misunderstood) features in the platform: Neighborhood Data and Market Dashboards.

The conversation starts with a familiar host fear—“I was way more booked this time last year… should I be worried?”—and quickly turns into a data-driven framework for answering that question without panic-cutting prices.

Luke shares how to compare current market occupancy vs. last year, how to tell whether demand is simply arriving later, and how to decide when to prioritize occupancy sensitivity vs. price sensitivity. Using real examples from White Birch Cabin, they break down how holidays like Juneteenth, school calendars, and changing lead times can quietly reshape demand.

The episode also explores:

• Why being one of the last listings to book during peak season can be a strategic advantage
• How to position your pricing in the lower third of your comp set to capture bookings without racing to the bottom
• When high early bookings are actually a signal that your rates may still be too low
• How to use the Competitor Calendar to see real minimum stays and pricing strategies side-by-side

They also compare PriceLabs data with AirDNA, explaining why AirDNA works well for high-level market validation while PriceLabs excels at real-world pricing decisions based on live comps.

If you’ve ever opened PriceLabs, tweaked a few numbers, and closed it again hoping for the best—this episode shows you where the real leverage lives.

00:00 – Welcome back & why this episode exists
01:10 – Reviewing White Birch Cabin inside PriceLabs
02:00 – Why market dashboards matter more than calendar tweaks
03:20 – Comparing your bookings vs. market occupancy
04:35 – Understanding demand lag vs. demand decline
05:40 – Pricing in the middle vs. top of your comp set
06:30 – June demand spike & the Juneteenth effect
08:40 – When not to lower prices—even if you’re nervous
10:00 – Using historical occupancy to predict future demand
11:00 – Competitor calendars & minimum stay strategies
12:40 – Seven-night vs. short stays: who’s really winning
13:10 – July peak pricing & being one of the last to book
15:00 – Early bookings as a signal you underpriced
16:35 – AI Insights: helpful shortcut or confirmation bias?
18:15 – Tutorials baked into PriceLabs (use them)
19:45 – PriceLabs vs. AirDNA: when to use each
21:10 – Final thoughts & where hosts should spend their time

The information provided in this episode is for educational and informational purposes only and should not be considered financial, legal, or tax advice. Pricing strategies, revenue results, and market performance vary by property, location, and individual circumstances. Always do your own research and consult with qualified professionals before making investment or pricing decisions.

📝 Episode Summary

In this episode of the Peak Season Podcast, Tyler and Lucas unpack one of the most debated levers in vacation‑rental strategy: Should you hold firm to a seven‑night minimum during peak season, or open the calendar to shorter stays to fill gap nights?

They explore how each approach affects revenue, workload, guest satisfaction, and operational flow, weaving in real examples from their own portfolios. The conversation also highlights the importance of active pricing, the role of professional revenue managers, and how understanding guest psychology can dramatically improve booking outcomes.

🔑 Keywords

vacation rental, seven‑night minimum, revenue management, property management, guest satisfaction, pricing strategy, gap nights, STR operations

💡 Top Takeaways

• Seven‑night minimums create stability but can reduce flexibility and limit booking opportunities.

• Shorter stays boost occupancy and review velocity, which can improve search ranking and visibility.

• Active pricing is non‑negotiable for maximizing revenue in competitive markets.

• Professional revenue managers can unlock hidden profit by monitoring trends and adjusting rates daily.

• Guest psychology matters — understanding how families, couples, and last‑minute travelers behave helps shape smarter policies.

• Operational logistics drive strategy, especially when it comes to cleaning schedules and turnover capacity.

• Consistency in management practices leads to smoother operations and better guest experiences.

• Competitor research reveals what’s working in your market and where you can differentiate.

• Flexible booking policies can widen your funnel and attract more qualified guests.

• Balancing workload with revenue is essential for long‑term sustainability and host sanity.

⏱️ Chapters

00:00:00 — 🎧 Introduction & Topic Overview

Setting the stage for the seven‑night minimum vs. short‑stay debate.

00:00:00 — 💵 Revenue & Booking Strategies

How minimum stays influence revenue, occupancy, and search performance.

00:00:00 — 🧹 Logistics & Management

Turnovers, cleaning schedules, and the operational realities behind stay rules.

00:00:00 — 📊 Pricing & Revenue Management

Why active pricing matters and how pros optimize your calendar.

00:00:01 — 🧠 Guest Psychology & Booking Policies

Understanding traveler behavior to set smarter, more effective rules.

00:00:01 — 🔚 Conclusion & Final Thoughts

Final insights on balancing flexibility, revenue, and operational flow.

The Peak Season Podcast – Part 2 with Brandon Wood

In Part Two of our conversation, Brandon Wood goes deep on what actually powers a scalable short-term rental operation—without burning out or over-engineering too early.

We cover Brandon’s full tech stack (from PMS to insurance), how he thinks about outsourcing versus control, and why time is the real bottleneck most operators ignore. Brandon also shares real-world customer service stories that should’ve been one-star disasters—but turned into five-star wins, dinner included.

This episode is a practical, no-nonsense look at what works once you’re past your first couple of properties—and what not to take on, even when the money looks good.

00:00 – Intro: Part Two with Brandon Wood
00:48 – Scaling to 15 properties without losing sanity
01:07 – Airbnb & VRBO only: delaying direct bookings on purpose
02:30 – Hospitable as a PMS (and why AI messaging isn’t quite there yet)
03:45 – Custom reporting, Canva, and staying hands-on
04:30 – Task management and staying above water
05:10 – PriceLabs vs outsourced revenue management
06:10 – Buying back time with outsourced pricing
06:55 – Digital guidebooks & search ranking tools
07:30 – Guest damage insurance: why AirCover isn’t enough
07:52 – How guest-paid incidental insurance works
08:34 – Insurance integrations and claim workflow
10:00 – Outsourcing bookkeeping (and why it pays for itself)
11:45 – Cleaning platforms vs keeping great cleaners
13:12 – Collecting guest data before you’re “ready”
14:20 – Outdoor security, cameras, and real-world mountain problems
15:00 – Noise, smoke, and occupancy monitoring
15:53 – Auto-rebooting WiFi routers (a must-have for remote properties)
17:47 – Rapid fire: biggest win in hospitality
18:02 – Bear, broken windshield, and a five-star review
22:36 – Why bad situations create the best reviews
23:31 – Nightmare scenarios and emotional control
24:23 – Taking on too much (accidental GC lessons)
28:09 – Learning when to say no to clients
31:26 – Podcast recommendations for STR operators
33:37 – Book recommendations for business and life
35:16 – How to connect with Brandon

One of the simplest “why didn’t I do this sooner” upgrades for remote or rural properties.

Automatic WiFi Rebooter (Amazon):
https://www.amazon.com/Keep-Connect-Device-Automatic-Rebooter/dp/B0C6YCQ2ZV/

This device automatically power-cycles your router when the internet drops—often fixing issues before guests even notice. Especially useful for mountain, lake, and off-the-beaten-path markets.

The views and opinions expressed in this episode are those of the hosts and guests and do not constitute legal, financial, tax, or investment advice. All examples discussed are for informational and educational purposes only. Every short-term rental market, property, and investor situation is different—listeners should conduct their own due diligence and consult with qualified professionals before making business decisions.

In this episode of The Peak Season Podcast, Luke and Tyler sit down with Brandon Wood, founder of Adventure Nest, for a candid conversation about what it actually looks like to scale a short-term rental portfolio without losing your sanity—or your family in the process.

Brandon shares his journey from a demanding W2 career into full-time short-term rentals, including how he went from a single property to operating 11 high-quality STRs across multiple states. Rather than chasing door count, Brandon takes a deliberate quality-over-quantity approach—prioritizing strong operations, protected markets, and sustainable income over flashy amenities and constant expansion.

They also get real about masterminds and coaching groups (the good, the bad, and the expensive), why smaller accountability circles often outperform massive paid communities, and how too much “learning mode” can quietly become procrastination.

Brandon unpacks hard lessons from early investments, including buying in overly saturated markets, misreading post-COVID data, and trusting large property management companies that dramatically underperformed. Along the way, he explains why he now leans into regulation, how data shaped his decision-making, and what finally pushed him to leave his W2—without the dramatic walkout.

This is Part 1 of a two-part interview, setting the foundation for how Brandon thinks about time, money, family, and long-term scalability in the STR business.

Find Brandon - www.myadventurenest.com

Work with Tyler & Luke - www.upstreamvacations.com

• Why quality beats door count when building a long-term STR business
• How regulation can actually protect your revenue and asset
• Why most large property management companies underperform
• How small accountability groups can outperform expensive masterminds
• The danger of staying in “learning mode” too long
• What it really takes to replace a W2 with STR income
• Why setup is the hard part—and operations get easier with reps
• Co-hosting strategies Brandon used to land early clients

00:00 – Introduction & Guest Overview
01:54 – Brandon’s Entry Into Short-Term Rentals
05:42 – Masterminds: What Helped and What Didn’t
07:28 – Accountability, Networking, and Smaller Groups
10:15 – Learning vs. Execution (and When to Switch Gears)
12:50 – Brandon’s Background and W2 Career
13:19 – Early Successes and Costly Mistakes
20:34 – Building a Sustainable Portfolio
23:06 – Regulation as a Competitive Advantage
25:43 – Lessons from Tennessee & Saturated Markets
27:26 – Expanding Into New, Niche Markets
33:21 – Leaving the W2 World (Without the Drama)
37:20 – How Brandon Lands Co-Hosting Clients

In Part 2, Brandon goes deeper into his underwriting process, how he evaluates markets, and how he’s scaling co-hosting without building a bloated property management machine.

The information shared in this podcast is for educational and informational purposes only and should not be considered financial, legal, or tax advice. Every short-term rental business, market, and personal financial situation is different.

In this episode, Luke Miller and Tyler K break down the latest AirDNA 2026 Outlook and what it means for short-term rental owners, investors, and operators heading into the next cycle.

We unpack a rare convergence of market forces—falling mortgage rates, stabilizing home prices, and recovering travel demand—that could create one of the most attractive entry points the STR industry has seen in years. If you’ve been feeling whiplash from the past couple seasons, this episode brings clarity, context, and a little calm to the chaos.

Spoiler: the sky isn’t falling… but the smart money is getting more selective.

• Why AirDNA sees 2026 as a pivotal reset year for short-term rentals
• What really happened in 2025 (and why it felt so weird)
• How interest rates and housing affordability are quietly reshaping opportunity
• The difference between headline doom and on-the-ground data
• Where demand is strongest heading into the next growth cycle
• Why some investors exiting the market may actually be good news for you

• 📉 Mortgage rates easing + home prices stabilizing = real buying opportunities
• 📈 Demand rebounded in 2025, even as momentum softened late in the year
• 🏡 Occupancy is expected to rise modestly by the end of 2025
• 💰 ADRs have largely stabilized, with holidays propping up pricing
• 🚪 Some over-leveraged operators are exiting—creating less competition and better deals
• 🗓️ 2026 is shaping up as a prime entry window for disciplined investors
• 🌊 Mountain, lake, and coastal markets remain long-term demand winners
• 🔮 2027 could mark a broader economic and travel demand rebound

00:00 – Introduction to the AirDNA 2026 Outlook
01:44 – 2025 Recap: Demand, Occupancy, and Market Reality
06:09 – What 2026–2027 Could Actually Look Like
12:15 – The Economic Backdrop (Without the Doom Loop)
14:14 – Housing Affordability & Investor Opportunity
19:18 – How to Think About Timing the Market
25:45 – Final Thoughts: Positioning for the Next Cycle

The information shared in this podcast is for educational and entertainment purposes only. Luke Miller and Tyler K are not attorneys, accountants, or financial advisors, and nothing discussed on this show should be considered legal, tax, or investment advice. All investing involves risk, and listeners should conduct their own due diligence and consult with qualified professionals before making any financial or business decisions. Past performance does not guarantee future results.

In this solo episode of The Peak Season Podcast, Luke breaks down a practical, repeatable system for forecasting short-term rental revenue using PriceLabs and a simple spreadsheet. Instead of vague goals like “make more money,” Luke walks through how to set clear monthly revenue targets, track progress in real time, and adjust pricing strategy based on occupancy, seasonality, and lead times.

Using a real property in Northwest Michigan, Luke shows how treating pricing like a fitness goal—broken into daily and weekly actions—creates clarity, confidence, and far better results. If you’ve ever felt behind on revenue with no clear plan to catch up, this episode provides a concrete framework you can apply immediately.

• Why “I just want more bookings” is not a real pricing strategy
• Using PriceLabs portfolio analytics instead of gut feelings
• Reverse-engineering an annual revenue goal into monthly targets
• Accounting for owner stays, one-off events, and skewed data
• Occupancy-sensitive vs. price-sensitive months (and how to tell the difference)
• When to lower weekday rates to drive longer stays
• How to avoid starting the year in a revenue deficit
• Why most hosts feel behind even when they’re performing well

• Set monthly revenue goals, not vague annual hopes
• Track actuals vs. goals at least once or twice per month
• Use occupancy thresholds (50% / 75%) to decide when to chase bookings vs. hold price
• Be the first to lower prices in slow months—and the last in peak season
• Adjust weekday pricing strategically to win longer stays without discounting weekends
• Forecasting gives you clarity and confidence instead of reactive decision-making

• Hosts using or considering PriceLabs
• STR owners who hate feeling “behind” with no clear fix
• Hosts managing seasonal markets with large swings in demand
• Operators who want pricing decisions driven by data, not anxiety

This episode includes screen sharing and live examples on YouTube. If you want to see exactly how the spreadsheet is structured and how pricing decisions are made inside PriceLabs, the video version is highly recommended.

Most hosts price reactively. This episode shows how to price intentionally—with a plan, a scoreboard, and fewer emotional spirals during slow months. Progress beats panic.

The views, opinions, and information expressed in this podcast are for general informational and educational purposes only. They are not intended to be financial, legal, tax, or investment advice. Listeners should consult with their own professional advisors before making any decisions related to real estate investing or short-term rental operations. The hosts make no guarantees regarding outcomes or results discussed in this episode.

In this episode of The Peak Season Podcast, Luke shares a behind-the-scenes look at what it really takes to launch a short-term rental at warp speed. From the closing table to live in just six days — and from over 1,000 miles away — this was not a smooth, Instagram-worthy rollout.

Between delayed closings, Midwest blizzards, scattered Wayfair boxes, canceled deliveries, marathon sourcing trips, and a smart lock that absolutely refused to cooperate, Luke breaks down the lessons learned the hard way while launching Northwoods Treehaus just days before Christmas.

Alongside Tyler, the conversation dives into what worked, what didn’t, and what Luke would never do again. If you’re setting up your first property, managing remotely, or feeling pressure to rush a launch, this episode is a reality check — and a roadmap — rolled into one.

👉 Check out the newest listing:
https://www.airbnb.com/h/northwoodstreehaus

(And yes — liking it and hitting the heart helps more than you think.)

00:00 – Intro: Launch windows and holiday chaos
00:52 – From closing table to live in six days
02:08 – Boxes in the snow before owning the house
03:26 – Lesson #1: Why scheduled deliveries will betray you
04:45 – Boots on the ground, family help, and hiring labor
05:46 – Lesson #2: Rent the minivan (always)
07:05 – Tracking missing shipments and managing delays
08:10 – DIY photos, AI edits, and getting a listing live fast
08:57 – Where to source locally when Amazon fails
10:39 – Lesson #3: Buy local, save time and money
11:04 – Lesson #4: Set up Wi-Fi and locks first
12:10 – Schlage Encode problems and router reality checks
14:52 – Backup plans for access (and backup to the backup)
15:21 – Lesson #5: Don’t buy at year-end if you can avoid it
16:14 – Why a full week on site changes everything
17:55 – When paying for professional setup does make sense
19:49 – Hiring early, hiring often, and staying in your lane
21:20 – Lesson #6: Always plan a second trip
22:39 – Cleaner SOPs, videos, and systemizing after launch
23:41 – Soft-launching with friends before organic guests
24:28 – Sharing the listing and what’s coming next

The views and opinions expressed in this podcast are based on personal experience and are for informational and educational purposes only. This content does not constitute legal, financial, tax, or investment advice. Always consult with qualified professionals before making business or investment decisions. Operating short-term rentals involves risk, and individual results may vary.

In this episode of the Peak Season Podcast, Luke and Tyler break down the property management system Hospitable and how hosts can use it to streamline operations and elevate the guest experience. They cover automated messaging rules, review workflows, team communication, and smart home integrations, sharing practical tips from real hosting experience. Whether you manage one property or a growing portfolio, this episode offers actionable insights to help you save time, improve communication, and scale with confidence.

• How automated messaging improves guest experience and consistency
• Using Hospitable to manage reviews and guest communication efficiently
• Streamlining operations with team notifications and workflows
• Leveraging smart home integrations to save time and reduce issues
• Why testing and refining automation leads to better bookings and reviews

00:00 Introduction to Hospitable and PMS basics
05:20 Messaging automation and guest communication
10:18 Automated reviews and responses
16:42 Team management and operations
19:27 Smart home integrations
27:35 Final thoughts and what’s next